Josie's assignment also resembles the experiences of Cameron Crowe, who went back to his old high school at 21 and wrote a novel and screenplay based on his experience there, which eventually became the movie Fast Times at Ridgemont High (1982).
When Garry Marshall's character is speaking to his employees at the Chicago Sun-Times board room, he says, "I don't even know my own kids." His real life daughter, Kathleen Marshall, is sitting to his right when he's speaking.
It is an issue in the movie that Josie is considerably older than her "high school crush" Guy (she is supposed to be 25, while he would be about 17), but actually, Drew Barrymore is 2 years younger than Jeremy Jordan, the actor who plays Guy.
The main DVD menu is borrowed as a fake-out DVD intro for Fight Club as a reference to both the vandalism of project mayhem and the film's messages of anti-consumerism, anti-hollywood and anti-romance.
David Arquette stars alongside both Drew Barrymore and Marley Shelton; Arquette starred in all four Scream movies. Drew Barrymore starred in the first Scream whilst Marley Shelton reunited with Arquette in Scream 4 - 11 years later.
In the film Josie tells everyone that she's 25 years old, beforehand she reminds her brother Rob he's 23 years old. Therfore she's the older sibling by two years, off screen David Arquette is four years older than Drew Barrymore.
During the prom, a pregnant Mary and Joseph go to sit down at a table but they're sent away by the popular girls (Gibby, Kristen and Kirsten) saying there is no room. This is a reference to there being no rooms available at the inn during the birth of Jesus Christ.